1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 131731176, compound

HRID 237417Notes

Reaction equation

HRID 237417 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:5]([NH:7][C@H:8]([C:13]([OH:15])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6])[CH2:3][OH:4].[CH3:33][C:34]([NH:45][CH2:46][CH:47]([OH:63])[CH2:48][O:49][C:50]1[C:55]2[C:56]3[C:61]([NH:62][C:54]=2[CH:53]=[CH:52][CH:51]=1)=[CH:60][CH:59]=[CH:58][CH:57]=3)([C:36]1[CH:41]=[CH:40][C:39]([N:42]=[N+:43]=[N-:44])=[CH:38][CH:37]=1)[CH3:35].[CH3:64][C:65]1[C@@H:82]([O:83][C:84]([C@H:86]([OH:103])[C@@H:87]([NH:94][C:95]([C:97]2[CH:98]=[CH:99][CH:100]=[CH:101][CH:102]=2)=[O:96])[C:88]2[CH:89]=[CH:90][CH:91]=[CH:92][CH:93]=2)=[O:85])[CH2:81][C@:77]2([OH:104])[C:78]([CH3:80])([CH3:79])[C:66]=1[C@@H:67]([O:122][C:123]([CH3:125])=[O:124])[C:68]([C@@:70]1([CH3:121])[C@H:75]([C@@H:76]2[O:105][C:106]([C:108]2[CH:109]=[CH:110][CH:111]=[CH:112][CH:113]=2)=[O:107])[C@:74]2([O:116][C:117]([CH3:119])=[O:118])[CH2:114][O:115][C@@H:73]2[CH2:72][C@@H:71]1[OH:120])=[O:69].C1CCN2C(=NCCC2)CC1>C1COCC1>[NH2:1][C@H:2]([C:5]([NH:7][C@H:8]([C:13]([OH:15])=[O:14])[CH2:9][CH:10]([CH3:11])[CH3:12])=[O:6])[CH2:3][OH:4].[CH3:35][C:34]([NH:45][CH2:46][CH:47]([OH:63])[CH2:48][O:49][C:50]1[C:55]2[C:56]3[C:61]([NH:62][C:54]=2[CH:53]=[CH:52][CH:51]=1)=[CH:60][CH:59]=[CH:58][CH:57]=3)([C:36]1[CH:41]=[CH:40][C:39]([N:42]=[N+:43]=[N-:44])=[CH:38][CH:37]=1)[CH3:33].[CH3:64][C:65]1[C@@H:82]([O:83][C:84]([C@H:86]([OH:103])[C@@H:87]([NH:94][C:95]([C:97]2[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=2)=[O:96])[C:88]2[CH:89]=[CH:90][CH:91]=[CH:92][CH:93]=2)=[O:85])[CH2:81][C@:77]2([OH:104])[C:78]([CH3:79])([CH3:80])[C:66]=1[C@@H:67]([O:122][C:123]([CH3:125])=[O:124])[C:68]([C@@:70]1([CH3:121])[C@H:75]([C@@H:76]2[O:105][C:106]([C:108]2[CH:113]=[CH:112][CH:111]=[CH:110][CH:109]=2)=[O:107])[C@:74]2([O:116][C:117]([CH3:119])=[O:118])[CH2:114][O:115][C@@H:73]2[CH2:72][C@@H:71]1[OH:120])=[O:69]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 131731177HCID 131731177, compound

Product 1

HCID 131731176HCID 131731176, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

11 (0.1 g, 0.070 mmol) was treated with 1% DBU in THF (3 mL) for 45 seconds at room temperature and the product was precipitated by 1 M HCl in diethyl ether (200 mL) then it was purified on a silica gel column using chloroform/methanol (7:1) to afford 12 (75 mg, 89%) as a white powder. ESI-MS (5 kV, MeOH): m/z (%)=1225.1 (100) [M+Na]+; HPLC (230 nm): >95%.

Workup

  1. customthe product was precipitated by 1 M HCl in diethyl ether (200 mL)
  2. customit was purified on a silica gel column

Sources & evidence

ORD record
ord-19cabb8fbeb748948771f233c80370e1
Source dataset
uspto-grants-2014_02
Patent number
US08642555B2

Reaction notes

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